Process of preparing nitrils of aromatic alpha-oxyacids.



JOSEPH L. TURNER, oFrmmDELPnIA, rsxrgsymitfix. .xxo cm OF COLLINGSWOOD,NEW JERSEY, ASSIGXORS T To all whomit may concern:

Be it known that we, ,los PM L. 'lt'nxi-zu, a sub ect of the (zar ofRussia. and (n.unns

E. VAXDERKLEED, a citizen of the l'uitcd 5 States, residing, rcswctn'cly, in Philadel- .ghia, Pennsylvania, and Collingswood. .\'c\\' 5erscy, have invented ccrtain lmpl'oVcmc-nts in Processes of Preparing.\'itrils of Aromatic Alpha-Oxyacids, of which the following is aSpcciticatiull. i Our invcntion relates to the production o certain newsubstances which are chemicailv c \'anh \'drins ol' protocatechuic aldch\'dc or of its monomcth \'l ether, dimethyl cthcr., or the like.corresponding to the chclnlcal formula in which formula R stands for a h\'drogen atom, which may be replaced by an alkyl group.

\ The object of our invention is to provide a process for the productionof the above noted chcmical suhstanccs, which are colorless com-Lyounds, soluble in alcohol and less readily oliihle in other. Whenhcated with alkalics orcacids, these nitrils are decomposed into tlncorresponding alpha-oxy-acids and ammonia, and as intermediary productsthe cor- SD rcspondiuQ amids may he formed.

The process of producing the new compounds consists in treating theabove mentioned protocatechuie aldehyde or its others with sodiumbisulfite in such a nuumer as to produce an addition compound, which inturn is reacted upon with potassium cyanid, pret'crahly in solution.

.\s a specific example of the process, I00 5 gra msc-f protoca tcchuicaldchydc are warmed to to FU(. foronehourm a waterhath with .300

c. c. of a com'cntrated (-10%) solution of so-' The crystals of the,sodium bisultite pnztocatc lmic-aldehyde readily go into solutiom andupon cooling, the nitril of the alpha-oxyhoniopmtocatechule acidcrystallizes out.

Specification of Lettels Patent. 7 Application filed July -22,

Pat-stated Aug. 4, 1905;

1907. Serial 384375;

The reaction OCt't's-"G'EE-{i ma he reprcscritcd as follows? As anotherspotti :cation of our prorcss, 100 grams of v." '=1 are warmed on awater hath with .s cof a concentrated solution of sodium 311 i-1e for aperiod of 3 onc hour. l'nder flil5 cmnlitions'the crys- 1 tals ofvanillin go IITJIU' s lution, and there is precipitated ant additioncompound of sodium hisultite misc "cszaillin. (in (outing there isformed a so :nlid mass of crystais which a re tlltered otn an i-:3-pressure. use

crystals aretheik n'ritaamtcd with a little water, after which tihz-reis added a solution of St) grams of poeassizzn cyanid M150 cc. of water.The c; of the hisul'titevauillin then go I olutiou and on the surface ofthe lllil mrates in a. state of sullicient a which is the nitri l ofsimianmy-hommwanillic acid.

l. The process mt r '-;ssring hitrils of a10- inatic alpha-os vnlzichlconsists in Ic-acting upon a .-'tcchol .dcrivative -with sodiumhisuli'izrc E rcactihg upon the resulting compound oath a cj'anid,sunbstantiallv as dcscrfllnci l, lac process ti gprc matic alplia-oxya:cu'ls acting upon a pyrcam Sodium hisullite ire \t. an additi n cumpmupon said ('OIHPUL at; I stantially as dcsc I 3. The process 0 mg mtrxlsof mooi inatic alpha-oxy ac ach consists in miding 100 grams of a: g1'ru-r:ttcclxol dcrivati'rc to 500 c. c. of a. (Pull-("Efifitiillsolution of sodium hisultite, h i t 80 grams of potas i of water; andseptum i t nitril formed, so istiazzz 3' as described.

: In testimony wl: we have signed am I names to this specificawvn, inthe presenm of two subscribing wiznm.

JOSEPH L. EI RXEP;

" ,"msqTED'STATEs PATENT OFFI E I the same, adding cgamd m c cl. out theresultmg cnanLEs 21 YAXDERKLEED:\

Wxrrmu ii Bamuzr, JOS. II. KL-KY.

I Vi tncsscs'h p t i I t

